Family Friendly Fall Events in Portland


With September making it's grand appearance, Maine families are shifting gears to welcome the sights, sounds and celebrations of fall. 

From Oktoberfest to apple themed everything, September's weather makes it the ultimate autumn adventure. Not to mention it's a nice break from the chaos of the back to school season. 

There's no shortage of fun festivals, fairs and things to do in the greater Portland area. So gather up the family and check out some of these fun festivals to kick off the fall! 

Here's some of the September and October events in the Portland area that we can't wait to visit. 

Maine's Pumpkin Trail

From Labor Day through October, celebrate the arts, history and giant fruit with the Maine Maritime Museum, Farnsworth Art Museum, Boothbay Railway Village and Damariscotta Pumpkinfest and Regatta. Maine's Pumpkin Trail covers 50 miles of Maine's most charming coastline and features cruises, train rides, giant racing pumpkin boats, parades, street art, flying & smashing pumpkins, and events for the entire family. Who says September is too early for pumpkins? For more information you can visit their Facebook page. 

Fall Foliage Festival

 Every Columbus Day Weekend the Museum's Village Green welcomes dozens of vendors of handmade items and fabulous food along with a wide variety of live entertainment at the annual Fall Foliage Festival. The sound of the train's steam whistle resonating throughout the crisp fall air reminds guests that this is not your typical craft show. 

Rides on the narrow gauge steam train and the opportunity for guests to explore exhibits detailing Maine's railroad heritage, interpreting village life, and displaying more than 60 antique automobiles set this event apart. Artisan demonstrations, live music and a children's corner adds to the fun of this family tradition. Sign up to enter the Pumpkin Carving Contest with lots of really great prizes for all ages and abilities. It's just $5 to register per person and that includes admission and your 10 to 12 pound pumpkin to carve and keep.

Swine & Stein Octoberfest

The annual Swine & Stein Octoberfest is a trifecta of beer, food, and music. Last year, a beer tasting showcased the incredible diversity and quality of Maine craft beers. In celebration of local Maine agriculture, fine restaurants and local food vendors from Gardiner and across the state served up a variety of interesting culinary dishes featuring local pork along with other quality menu items. Adding to the festivities, a line-up of favorite and emerging Maine bands entertained throughout the day. A unique array of games and activities, with some fun fall prizes.

Don't miss out on this outdoor festival in the setting of one of Maine's most charming main streets! In addition to beer, pork, and music, there will be a number of ongoing activities, including in past years a chicken fling, frozen T-shirt race, and the annual Maine rock, paper, scissors championship and the annual Gardiner Beard & Mustache Competition. This family-friendly event also offers pumpkin carving and other children's activities. 

There's so many events popping up in Maine over the next few months we can't pick just one.

The Portland area is at the forefront of the food, music and craft boom in the northeast and the changing of the seasons truly gives them an opportunity to shine. Whether you're local or just visiting, you'll have tons of opportunities to kick off the fall to the fullest.